Glycinol (pterocarpan)

Glycinol

Names
Preferred IUPAC name

(6aS,11aS)-6H-[1]Benzofuro[3,2-c][1]benzopyran-3,6a,9(11aH)-triol

Identifiers

CAS Number

* 69393-95-9 N

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:15649

ChemSpider |

* 114790 N

KEGG |

* C01263

PubChem CID

* 129648

UNII |

* Q0O9HGR94O

InChI

* InChI=1S/C15H12O5/c16-8-1-3-10-12(5-8)19-7-15(18)11-4-2-9(17)6-13(11)20-14(10)15/h1-6,14,16-18H,7H2/t14-,15+/m0/s1 N

Key: QMXOFBXZEKTJIK-LSDHHAIUSA-N N

* InChI=1/C15H12O5/c16-8-1-3-10-12(5-8)19-7-15(18)11-4-2-9(17)6-13(11)20-14(10)15/h1-6,14,16-18H,7H2/t14-,15+/m0/s1

Key: QMXOFBXZEKTJIK-LSDHHAIUBH

SMILES

* O3c1c(ccc(O)c1)[C@@H]4Oc2cc(O)ccc2[C@]4(O)C3

Properties

Chemical formula

| C15H12O5
Molar mass | 272.25 g/mol

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N verify (what is YN ?)
Infobox references

Tracking categories (test):

* SizeSet

Glycinol is a pterocarpan, a type of natural phenol. It is a phytoalexin found in the soybean (Glycine max). It is formed by the cyclisation of daidzein.[citation needed]

More recent literature supports that glycinol has potent phytoestrogenic activity.[1][2]

The so-called osteogenesis that is causes is postulated to be a preventative factor for osteoporosis.[citation needed]

It can be synthethised chemically and possesses two chiral centers.[3]

Glycinol is the direct precursor of glyceollins through the action of a prenyltransferase.[citation needed]

Experiments show that the 6a oxygen of glycinol is derived from molecular oxygen.[4]

## References

1. ↑ Boué, Stephen M.; Tilghman, Syreeta L.; Elliott, Steven; Zimmerman, M. Carla; Williams, K. Y.; Payton-Stewart, Florastina; Miraflor, Allen P.; Howell, Melanie H. et al. (2009). "Identification of the Potent Phytoestrogen Glycinol in Elicited Soybean (Glycine max)". Endocrinology 150 (5): 2446–2453. doi:10.1210/en.2008-1235. ISSN 0013-7227. PMID 19116342.
2. ↑ Strong, Amy L; Jones, Robert B; Glowacki, Julie; Boue, Stephen M; Burow, Matthew E; Bunnell, Bruce A (2017). "Glycinol enhances osteogenic differentiation and attenuates the effects of age on mesenchymal stem cells". Regenerative Medicine 12 (5): 513–524. doi:10.2217/rme-2016-0148. ISSN 1746-0751. PMID 28718749.
3. ↑ Luniwal Amarjit; Khupse Rahul S; Reese Michael; Lei Fang; Erhardt Paul W (2009). "Total Syntheses of Racemic and Natural Glycinol". Journal of Natural Products 72 (11): 2072–2075. doi:10.1021/np900509f. PMID 19943626. http://cat.inist.fr/?aModele=afficheN&cpsidt=22189893.
4. ↑ Matthews, David E.; Plattner, Ronald D.; Vanetten, Hans D. (1989). "The 6a oxygen of the pterocarpan glycinol is derived from molecular oxygen". Phytochemistry 28 (1): 113–115. doi:10.1016/0031-9422(89)85020-4. Bibcode: 1989PChem..28..113M. https://zenodo.org/record/1258250.

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Types of pterocarpans

Pterocarpans:|

* Erybraedin C
* Erythrabyssin II
* Folitenol
* Glycinol
* Maackiain
* Orientanol A, B and C
* Pisatin
* Sophorol
* Trifolirhizin

O-methylated|

* Kushenin
* Medicarpin
* Pterocarpin

Prenylated|

* Bitucarpin A and B
* Glyceollidin I and II
* Glyceollins (Glyceollin I, II, III and IV)
* Glycyrrhizol A
* Morisianine
* Phaseolin
* Striatine

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